WIN Spotlight: Fiona O’Leary Sloan

Welcome to the latest “WIN Spotlight,” our ongoing series that celebrates inspirational women in our community. Each interview features a member of WIN who is championing innovation at her organization or across the industry. We dig into the diverse perspectives, influences, mission, drivers, and dreams of these leaders, and of course, ask them for practical advice and pro tips from their years of experience.

This month we are excited to feature Fiona O’Leary Sloan, Business Designer at Doberman NY and WIN ambassador!

Who are you and what do you do?

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Hey there! I’m Fiona, and I currently work as a Business Designer at Doberman, an international design and innovation firm with offices in NYC and Stockholm. As a business designer, I combine design methodologies with business tools to solve real-world challenges for our clients. Outside of the office, I’m an intrepid traveler (ask me about the time I was bitten by a potentially rabid dog in Bangkok), a staunch hostel aficionado (I’ve stayed in over 150 hostels while visiting 52 countries), and a bonafide coffee snob (along with everyone else).

What’s the best part of your job?

Wearing a million hats. As the first (and still only) business designer at Doberman, it is my challenge and privilege to build out the discipline as part of our larger (and equally nascent) strategy offering. That means that every day brings a new adventure, whether it be building a venture pitch deck, conducting a market analysis, or organizing an event like the one we recently co-hosted with WIN.

What I love about business design more broadly is how it challenges the conventional notion of what business strategy means. When compared to traditional consulting, business design is more likely to embrace ambiguity, accept user and business needs as equal inputs, and take inspiration from unexpected sources—and I love that. Because at my core, I am driven by a firm belief that well-designed businesses can effect radical social change.

How do you define innovation? 

Innovation is about newness. It’s about putting new energy into something—a product, an industry, a business model—in order to reinvent the expected or create the altogether new. “Good” innovation takes things one step further, pushing the world forward to create a radically ambitious and inclusive future.

What is your favorite quotation?

I love myself.’ the quietest. simplest. most powerful. revolution. ever.
— Nayyirah Waheed

What is your inspiration - how do you keep up to date with the world? 

I listen to The Daily every morning to keep up to date with what everyone’s chatting about around the coffee machine, and because I’m a snob for high production-value podcasts (see also: Caliphate and More Perfect). My favorite newsletters are Dave Pell’s NextDraft for long-form articles on current events, and Jillian Richardson’s The Joy List for cool NYC events that are easy to attend solo.

What is the best advice someone has given you about your career? How did it help you?

Get good at quitting gracefully. Shortly after I graduated from college, I ended up working for a company that—it quickly became clear—didn’t resonate with my values. I knew I wanted to quit, but I had just signed a year-long lease in a brand-new city, and I felt like I was in too deep to get out. Enter Andrew Yang, then the CEO of Venture for America and still one of the highest-integrity people I know. Sitting across from me in a Detroit café, Andrew interlaced his fingers in his lap and said (and I’m paraphrasing): “Fiona, there’s something you’re going to have to get good at in your career—and that is the art of quitting gracefully. Think about it: quitting, like anything else, is a skill, and it’s one you have to practice. So let’s get to it.” And so I did. What Andrew taught me that day was invaluable: all things end, sometimes beautifully and sometimes not, but we can always try to end things with grace.

What is your advice for women in innovation and the next generation of female leaders?

  1. Go after opportunities that you seem under qualified for (men certainly do)

  2. Lift other women up at every opportunity

  3. Be kind to yourself, always

What did you study that led you into innovation?

I studied anthropology in undergrad, and subsequently returned to the classroom to get a Masters in Public Service and an MBA. I think that what led me to each of those degrees is the same thing that led me to innovation: my interest in people.

What product, service, or industry do you think is most ripe for innovation? Why?

Civic engagement and governance. In the wake of the Iowa caucus fiasco, it’s more clear than ever before that there’s a massive need for us to rethink the ways we can use technology and design to bolster our democracy. I’m inspired by organizations like Code for America, and can’t wait to see even more innovations in this space.

How is New York unique in how it does innovation?

One of the most unique things about New York in general is, somewhat ironically, the MTA. For all my gripes with our subway system, it holds the diversity of the city together—people of all backgrounds intersect, and are humbled, by our fair MTA. And that unintentional shared experience is what makes the innovation ecosystem here unique, as well: it’s (slightly) less insular and isolated from everyday realities when compared to cities like San Francisco.

What are some of your favorite women owned businesses/brands to support? 

So many! I’m obsessed with Moorea Seal, a Seattle-based boutique that features amazing women-led brands like Malicious Women Candle Co. and Hello Zephyr. For paper goods, I love Ferme à Papier — I’m a big believer in handwritten thank you notes, and these ones from founder Cat Seto are my favorites. Clothing-wise, I love brands that bake size inclusivity into their DNA — especially Universal Standard, Parade, and Girlfriend Collective. And for take-your-life-with-you purses, Cuyana is my go-to.

Thank you Fiona for sharing your story with the WIN community!


Photos by Marcela Madera

Edited by Marcela Madera

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